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O'Brien is a member of the Inner Party and, like Winston Smith, works in the Ministry of Truth. There, he holds a senior position that is so distant that Winston has only a vague idea of its nature. Winston suspects that O'Brien secretly opposes the Party. Eventually O'Brien approaches Winston with some leading remarks which seem to confirm Winston's suspicions. Winston finds the courage to approach him candidly, declaring himself an enemy of the totalitarian state. At first, Winston's intuition seems to be correct: O'Brien presents himself as a member of the "Brotherhood" seeking to overthrow the Party and INGSOC. O'Brien invites Winston (who then invites Julia) to his flat where, as a member of the Party elite he lives in comparative luxury. There he extracts a series of pledges from the couple that they are prepared to do anything to serve the Brotherhood, except (at Julia's protest) to separate from each other.

In truth, O'Brien is an agent of the Thought Police, and is completely loyal to the Party and to Ingsoc. He is part of a false flag resistance movement whose goal is to find thought-criminals (citizens who think something that is deemed to be unacceptable by the Party), lure them in by pretending to be on their side, then arrest and "cure" them.

O'Brien is next seen after Winston is arrested by the Thought Police. He reveals himself as he enters the cell by responding to Winston's exclamation, "They've got you too!", by wryly commenting, "They got me a long time ago."

Over several weeks, O'Brien tortures Winston to cure him of his "insanity," in particular his "false" notion that there exists a past and an external, self-evident reality independent of the Party; O'Brien explains, that reality is simply whatever the Party says it is.

He is entirely honest about the brutal cynicism of the Party; the Party does not seek power to do anything good, but simply to revel in that power: "Always, Winston, at every moment, there will be the thrill of victory, the sensation of trampling on an enemy who is helpless. If you want a picture of the future, imagine a boot stomping on a human face — forever."

Even in the torture scenes, there is a strange intimacy that persists between Winston and O'Brien. O'Brien even states that Winston's mind appeals to him, and that it resembles his own mind, except that Winston happens to be "insane." Eventually, in Room 101, O'Brien tortures Winston into submission so that he "willingly" embraces the philosophy of the Party.

The choice of the clearly Irish surname is regarded as a reference to Brendan Bracken, 1st Viscount Bracken, under whom Orwell worked during the war creating propaganda, and whom Orwell detested. In what has been described as "one of the strangest coincidences in literature", it was revealed in 2003 that O'Brien was the codename of NKVD agent Hugh O'Donnell, who received reports on the author from his subordinate David Crook when Crook spied on Orwell during the Spanish Civil War.[2]